Dimethylformamide → (2,4-Difluoro-3-formyl-phenyl)-carbamic acid tert-butyl ester

HRID 1964980Notes

Reaction equation

HRID 1964980 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=1[F:15])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.C([N-]C(C)C)(C)C.[Li+].CN(C)[CH:32]=[O:33]>O1CCCC1>[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[C:10]([CH:32]=[O:33])[C:9]=1[F:15])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 2724682Lithium diisopropylamideHCID 22986665Tert-butyl (2,4-difluorophenyl)carbamateHCID 178418339Butyllithium

Product 1

HCID 58086596(2,4-Difluoro-3-formyl-phenyl)-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2,4-difluoro-phenyl)-carbamic acid tert-butyl ester (123, 1.41 g, 6.17 mmol) in tetrahydrofuran (60.0 mL) under an atmosphere of nitrogen at 78° C. were added n-butyllithium (2.50 M in hexane, 2.59 mL) for 30 min. Lithium diisopropylamide (2.0 M in hexane, 3.4 mL) was added to the reaction. After 35 min, N,N-dimethylformamide (1.05 mL, 0.0136 mol) was added to the reaction mixture. The reaction was allowed to cool to room temperature overnight. The organic layer was washed with brine, dried over sodium sulfate, concentrated and purified by silica gel chromatography, eluting with 20% ethyl acetate in hexane to provide compound 124.

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. custompurified by silica gel chromatography
  5. washeluting with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-b818de35d6b3485f9327345dcd56453a
Source dataset
uspto-grants-2013_04
Patent number
US08415469B2

Reaction notes

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